CN107903365A - A kind of urea phenolic resin crosslinking agent and its synthetic method - Google Patents
A kind of urea phenolic resin crosslinking agent and its synthetic method Download PDFInfo
- Publication number
- CN107903365A CN107903365A CN201711046654.8A CN201711046654A CN107903365A CN 107903365 A CN107903365 A CN 107903365A CN 201711046654 A CN201711046654 A CN 201711046654A CN 107903365 A CN107903365 A CN 107903365A
- Authority
- CN
- China
- Prior art keywords
- urea
- formaldehyde
- phenolic resin
- crosslinking agent
- phenol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
- C08G14/06—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols and monomers containing hydrogen attached to nitrogen
- C08G14/08—Ureas; Thioureas
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/50—Compositions for plastering borehole walls, i.e. compositions for temporary consolidation of borehole walls
- C09K8/504—Compositions based on water or polar solvents
- C09K8/506—Compositions based on water or polar solvents containing organic compounds
- C09K8/508—Compositions based on water or polar solvents containing organic compounds macromolecular compounds
- C09K8/512—Compositions based on water or polar solvents containing organic compounds macromolecular compounds containing cross-linking agents
Abstract
The present invention provides a kind of urea phenolic resin crosslinking agent, adds urea reaction after being reacted by formaldehyde and phenol under base catalyst effect and obtains, wherein, the molar ratio of formaldehyde and phenol is 34：1, the molar ratio of the molal quantity total amount and urea of phenol and formaldehyde is 45：1, catalyst amount accounts for formaldehyde, phenol, the 0.2 0.5% of urea three's quality sum.Phenolic resin is modified using urea, synthesize urea phenolic resin crosslinking agent, on the one hand the quantity of active group in phenolic resin crosslinking agent is reduced, prevents the curing of urea phenolic resin, improves the stability of urea phenolic resin, on the other hand, phenolic resin is modified with urea, makes urea excessive, consumes excessive formaldehyde, formaldehyde is not discharged during storage, transport, use, reaches the requirement of environmental protection.
Description
Technical field
The invention belongs to technical field of oilfield chemistry, and in particular to a kind of urea phenolic resin crosslinking agent and its synthetic method.
Background technology
For Changqing oilfields anisotropism it is serious, there is crack and macropore or layer intrinsic permeability to differ larger oil reservoir, use
Polymer gel profile control agent processing near wellbore stratum, can effectively block selected stratum, improve the injection pressure of water injection well.Phenol
The crosslinked polymer gel profile control agent of urea formaldehyde has good temperature resistance and mobility, temperature in use up to 90 DEG C, be not easy by
The influence of oil reservoir mineral physics chemical action, gel strength is easy to control, can keep mobility and injectability for a long time.
It has dynamic spread effect in the earth formation, and can expand swept volume and improve oil displacement efficiency, meets Changqing oilfields water injection well
The requirement of profile control.
The crosslinking agent of polymer gel profile control agent is typically chosen phenolic resin, but phenolic resin crosslinking agent is scarce there are two
Point：First, there are more active group in phenolic resin crosslinking agent molecule, the resting period is long at high temperature, after may causing
Continuous curing reaction, loses cross-linking properties；Remaining formaldehyde is reacted second, existing in phenol resin solution so that phenolic resin is handed over
Joining agent, there are the problem of environmental pollution during storage, transport, use.
The content of the invention
The purpose of the present invention is overcoming above-mentioned technical problem existing in the prior art, urea phenolic resin crosslinking agent is improved
Stability, while improve the feature of environmental protection.
For this reason, the present invention provides a kind of urea phenolic resin crosslinking agent, by formaldehyde and phenol under base catalyst effect it is anti-
Should after add urea reaction and obtain, wherein, the molar ratio of formaldehyde and phenol is 3-4：1, the molal quantity total amount of phenol and formaldehyde
Molar ratio with urea is 4-5：1, catalyst amount accounts for formaldehyde, phenol, the 0.2-0.5% of urea three's quality sum.
The base catalyst is sodium hydroxide.
Present invention also offers a kind of synthetic method of urea phenolic resin crosslinking agent, comprise the following steps：
Step 1）First the phenol of formula ratio is poured into reactor, base catalyst is divided into two parts, two parts of mass ratioes are 2:1, then
Added after more a base catalyst is dissolved with water in reactor, post-reactor be put into 70-90 DEG C of water bath with thermostatic control, stir
Mix reaction 15-25min；
Step 2）The formaldehyde of formula ratio is divided into mass ratio for 4:Two parts of 1, add more one large formaldehyde in reactor, in 70-
Continue stirring reaction 35-40min in 90 DEG C of water bath with thermostatic control；
Step 3）Add in reactor, stirred in 70-90 DEG C of water bath with thermostatic control anti-after another base catalyst is dissolved with water
Answer 15-25min；
Step 4）Another formaldehyde is added in reactor, the stirring reaction 15-25min in 90 DEG C of waters bath with thermostatic control；
Step 5）The urea of formula ratio is added, stirring reaction 15-25min, obtains orange-red liquid in 90 DEG C of waters bath with thermostatic control,
It is drying to obtain.
The molar ratio of formaldehyde and phenol is 3:1, catalyst amount accounts for formaldehyde, phenol, the 0.3% of urea three's quality sum,
The molar ratio of the molal quantity total amount and urea of phenol and formaldehyde is 4.2：1.
Present invention also offers a kind of profile control agent, including urea phenolic resin crosslinking agent, cationic polyacrylamide is further included
And water, wherein, the mass percent of three is respectively：Cationic polyacrylamide 0.15%-0.6%, urea phenolic resin crosslinking agent
0.2-0.3%, remaining is water.
The cationic polyacrylamide cationic polymerization degree is more than 10%, and relative molecular weight is more than 5,000,000.
The beneficial effects of the invention are as follows：The present invention is modified phenolic resin with urea, the phenolic resin crosslinking of synthesis urea
Agent, on the one hand reduces the quantity of active group in phenolic resin crosslinking agent, prevents the curing of urea phenolic resin, improves urea phenolic aldehyde tree
The stability of fat, on the other hand, is modified phenolic resin with urea, makes urea excessive, consumes excessive formaldehyde, storing up
Deposit, transport, formaldehyde is not discharged during use, reach the requirement of environmental protection.
The urea phenolic resin crosslinking agent water solubility is more than 25%, free formaldehyde content 0.80%, with cationic polyacrylamide
Gel-type profile control agent is cross-linked to form, forms within 4~5 days high deformation gel, gel strength is up to 300000mPas.
It will be described in further details below.
Embodiment
Embodiment 1：
A kind of urea phenolic resin crosslinking agent is present embodiments provided, is added again after being reacted by formaldehyde and phenol under base catalyst effect
Enter urea reaction to obtain, wherein, the molar ratio of formaldehyde and phenol is 3-4：1, the molal quantity total amount and urea of phenol and formaldehyde
Molar ratio is 4-5：1, catalyst amount accounts for formaldehyde, phenol, the 0.2-0.5% of urea three's quality sum.
The present invention is modified phenolic resin with urea, synthesizes urea phenolic resin crosslinking agent, on the one hand reduces phenolic aldehyde tree
The quantity of active group in fat crosslinking agent, prevents the curing of urea phenolic resin, improves the stability of urea phenolic resin, the opposing party
Face, is modified phenolic resin with urea, makes urea excessive, consumes excessive formaldehyde, in storage, transport, uses process
In do not discharge formaldehyde, reach environmental protection requirement.
Embodiment 2：
On the basis of embodiment 1, a kind of synthetic method of urea phenolic resin crosslinking agent, including following step are present embodiments provided
Suddenly：
Step 1）First the phenol of formula ratio is poured into reactor, base catalyst is divided into two parts, two parts of mass ratioes are 2:1, then
Added after more a base catalyst is dissolved with water in reactor, post-reactor be put into 70-90 DEG C of water bath with thermostatic control, stir
Mix reaction 15-25min；
Step 2）The formaldehyde of formula ratio is divided into mass ratio for 4:Two parts of 1, add more one large formaldehyde in reactor, in 70-
Continue stirring reaction 35-40min in 90 DEG C of water bath with thermostatic control；
Step 3）Add in reactor, stirred in 70-90 DEG C of water bath with thermostatic control anti-after another base catalyst is dissolved with water
Answer 15-25min；
Step 4）Another formaldehyde is added in reactor, the stirring reaction 15-25min in 90 DEG C of waters bath with thermostatic control；
Step 5）The urea of formula ratio is added, stirring reaction 15-25min, obtains orange-red liquid in 90 DEG C of waters bath with thermostatic control,
It is drying to obtain.
（1）Phenol is with formaldehyde mole ratio on the water miscible influence of urea phenolic resin crosslinking agent
Since formaldehyde has penetrating odor, and with the increase of formaldehyde dosage, reaction is fierce, is difficult to control, and selects formaldehyde：Phenol
Molar ratio is respectively 1.5,2,3,4 to be tested, and the solubility of urea phenolic resin crosslinking agent is measured at 20 DEG C, is shown in Table 1.
The solubility of urea phenolic resin crosslinking agent under the different formaldehyde-phenol molar ratios of table 1
As shown in table 1, as formaldehyde and phenol molar ratio increase, water solubility first increases to be reduced afterwards, the reason is that hydroxymethyl phenol increases,
Solubility increase, but as hydroxymethyl phenol molecular concentration increases, there is three-dimensional-structure in intermolecular generation polycondensation reaction, makes water solubility
Decline.General formaldehyde dosage should not be excessive, and excessive formaldehyde does not participate in reaction, easily causes the influence of environment.Formaldehyde, phenol mole
Than for 3：1 is optimal.
（2）Catalyst is on the water miscible influence of urea phenolic resin crosslinking agent
Select NaOH to be tested as catalyst, measure the solubility of urea phenolic resin crosslinking agent under different catalysts dosage, see
Table 2.
2 catalyst dosage of table is on the water miscible influence of urea phenolic resin crosslinking agent
It is, in general, that the condensation degree of dissolved of urea phenolic resin crosslinking agent is not high, and if the catalyst alkalescence used is stronger, the urea phenol of generation
The content of methylol is higher in urea formaldehyde cross-linker molecules, the appropriate dosage for increasing catalyst, it helps the life of hydroxymethyl phenol
Into the water solubility of raising urea phenolic resin crosslinking agent.
（3）Reaction temperature is on the water miscible influence of urea phenolic resin crosslinking agent
As temperature raises, the urea phenolic resin crosslinking agent of synthesis can further be polymerize, and be become by linear urea phenolic resin
Build urea phenolic resin, so as to influence water solubility, selects 50 DEG C, and 60 DEG C, 70 DEG C, 80 DEG C, 90 DEG C are tested, and measures urea phenolic aldehyde
The solubility of resin cross-linking agent, is shown in Table 3.
Influence of 3 reaction temperature of table to urea phenolic resin crosslinking agent solubility
As shown in table 3, the urea phenolic resin crosslinking agents of 70 DEG C of synthesis are water-soluble preferably, but in view of catalyst is highly exothermic and work
The influence of the objective condition such as industry synthesis, maximum temperature is no more than 90 DEG C, but maintains 70 DEG C as far as possible and tested.Reaction temperature is got over
Low, self-condensation reaction speed is slower；When temperature is more than 90 DEG C, polynary hydroxymethylphenol polycondensation and forms build knot quickly
Structure, glue viscosity steeply rise, while are changed into urea phenolic resin not soluble in water.
（4）Reaction time is on the water miscible influence of urea phenolic resin crosslinking agent
Although the addition reaction speed of formaldehyde and phenol is much larger than the polycondensation reaction speed of polynary hydroxymethylphenol, in order to obtain
Water miscible first rank urea phenolic resin is obtained, reaction temperature and time must be strictly controlled.Reaction time is crosslinked urea phenolic resin
The water miscible influence of agent is shown in Table 4.The reaction time refers to the total reaction time of whole building-up process.
Influence of 4 reaction time of table to urea phenolic resin crosslinking agent solubility
As shown in table 4, by rationally controlling the reaction time, the water solubility of urea phenolic resin crosslinking agent can be improved.Control reaction
Time can obtain the urea phenolic resin crosslinking agent of good aqueous solubility for 120min.
（5）Urea dosage is on the water miscible influence of urea phenolic resin crosslinking agent
Selection（Phenol+formaldehyde）：The molar ratio of urea is respectively 3.5,4,4.2,4.5,5 to be tested.Measure the urea phenol of synthesis
The dissolubility of urea formaldehyde crosslinking agent, is shown in Table 5.
Influence of 5 urea of table to urea phenolic resin crosslinking agent solubility
As shown in table 5, amount of urea is different, and water solubility differs greatly, and selects（Phenol+formaldehyde）：Urea=4.2（Molar ratio）, close
Into urea phenolic resin crosslinking agent solubility it is maximum.
Embodiment 3：
On the basis of embodiment 2, a kind of synthetic method of urea phenolic resin crosslinking agent, specific practice are present embodiments provided：
By formaldehyde：Phenol=3：1 (molar ratio) weighs phenol, pours into three-necked flask；Sodium hydroxide is weighed in 0.3% ratio, and
0.2% and 0.1% two part is classified as, first 0.2% sodium hydroxide is dissolved in the constant temperature for inserting 70 DEG C is poured into after three-necked flask after water
In water-bath, stirring reaction 20 minutes, triggers the catalysis of the phenol alkalescence first step；The formaldehyde for accounting for formaldehyde gross weight 80% is added, it is permanent
70 DEG C of temperature continues stirring reaction 40 minutes；Then the sodium hydroxide of residue 0.1% is dissolved in after water and pours into three-necked flask, constant temperature 70
Continue stirring reaction 20 minutes after DEG C；Remaining 20% formaldehyde is eventually adding, is warming up to 90 DEG C, stirring reaction 20 minutes；Press（Benzene
Phenol+formaldehyde）：Urea is 4.2：1（Molar ratio）Urea is added, keeps 90 DEG C of temperature, stirring reaction 20 minutes, obtains orange-red
Liquid, it is dry, it is urea phenolic resin crosslinking agent.
Wherein, sodium hydroxide be dissolved in water water make sodium hydroxide dissolve, drying time in hypervolia later stage length.
Embodiment 4：
On the basis of embodiment 3, a kind of profile control agent, including urea phenolic resin crosslinking agent are present embodiments provided, further includes sun
Cationic polyacrylamide and water, wherein, the mass percent of three is respectively：Cationic polyacrylamide 0.15%-0.6%, urea
Phenolic resin crosslinking agent 0.2-0.3%, remaining is water.
（1）The cross-linking properties evaluation of urea phenolic resin crosslinking agent
70 DEG C of Changqing oilfields formation temperature is simulated, profile control agent prescription is water-soluble for 0.15%-0.6% cationic polyacrylamide+0.3%
Property urea phenolic resin crosslinking agent, remaining is water flooding.Cationic polyacrylamide cationic polymerization degree is more than 10%, and molecular weight is big
In 5,000,000.Viscosity after its profile control agent plastic is measured using BROOKFIELD DV-III ULTRA rotary viscometers, selects No. 64
Rotor, setting speed 1, the viscosity of profile control agent is shown in Table 6 after gelation time and plastic.
The performance of 6 gel-type profile control agent of table
As shown in table 6, with cationic polyacrylamide（Polymer is referred to as in table 6）For host agent, the urea phenolic resin of synthesis
Crosslinking agent（Crosslinking agent is referred to as in table 6）The profile control agent of preparation, just can in 70 DEG C of simulated formation under confined conditions for 4~5 days
High deformation gel is formed, and shows preferable gel strength, gel minimum intensity reaches 48100mPas, and highest can reach
To 300000mPas, it can meet the requirement of Changqing oilfields difference oil reservoir profile control.
（2）The free formaldehyde content measure of urea phenolic resin crosslinking agent
Using the free formaldehyde content of titration measuring urea phenolic resin crosslinking agent, 5.000g samples are weighed, add 50mL distilled water
Dissolving, adds the hydrochloric acid 10.00mL and thymolphthalein indicator 15-20 drops of 15% sodium sulfite solution 20mL, 0.5mol/L,
Vibration, with the sodium hydroxide titration of 0.5mol/L, makees blank test, calculates free formaldehyde content, be shown in Table 7.
7 urea phenolic resin crosslinking agent free formaldehyde content of table
By measuring, free formaldehyde content average out to 0.80% in the urea phenolic resin crosslinking agent of synthesis.
Above example belongs to the common knowledge and known technology of the art without the part specifically described, herein
No longer describe in detail one by one.
The foregoing examples are only illustrative of the present invention, does not form the limitation to protection scope of the present invention, all
It is to be belonged to the same or similar design of the present invention within protection scope of the present invention.
Claims (6)
- A kind of 1. urea phenolic resin crosslinking agent, it is characterised in that：Add again after being reacted by formaldehyde and phenol under base catalyst effect Enter urea reaction to obtain, wherein, the molar ratio of formaldehyde and phenol is 3-4：1, the molal quantity total amount and urea of phenol and formaldehyde Molar ratio is 4-5：1, catalyst amount accounts for formaldehyde, phenol, the 0.2-0.5% of urea three's quality sum.
- A kind of 2. urea phenolic resin crosslinking agent according to claim 1, it is characterised in that：The base catalyst is hydroxide Sodium.
- 3. the synthetic method of a kind of urea phenolic resin crosslinking agent according to claim 1, it is characterised in that including following step Suddenly：Step 1）First the phenol of formula ratio is poured into reactor, base catalyst is divided into two parts, two parts of mass ratioes are 2:1, then Added after more a base catalyst is dissolved with water in reactor, post-reactor be put into 70-90 DEG C of water bath with thermostatic control, stir Mix reaction 15-25min；Step 2）The formaldehyde of formula ratio is divided into mass ratio for 4:Two parts of 1, add more one large formaldehyde in reactor, in 70- Continue stirring reaction 35-40min in 90 DEG C of water bath with thermostatic control；Step 3）Add in reactor, stirred in 70-90 DEG C of water bath with thermostatic control anti-after another base catalyst is dissolved with water Answer 15-25min；Step 4）Another formaldehyde is added in reactor, the stirring reaction 15-25min in 90 DEG C of waters bath with thermostatic control；Step 5）The urea of formula ratio is added, stirring reaction 15-25min, obtains orange-red liquid in 90 DEG C of waters bath with thermostatic control, It is drying to obtain.
- A kind of 4. synthetic method of urea phenolic resin crosslinking agent according to claim 3, it is characterised in that：Formaldehyde and phenol Molar ratio be 3:1, catalyst amount accounts for the molal quantity of formaldehyde, phenol, the 0.3% of urea three's quality sum, phenol and formaldehyde Total amount and the molar ratio of urea are 4.2：1.
- 5. a kind of profile control agent, includes a kind of urea of the synthetic method synthesis of urea phenolic resin crosslinking agent as claimed in claim 3 Phenolic resin crosslinking agent, it is characterised in that：Cationic polyacrylamide and water are further included, wherein, the mass percent point of three It is not：Cationic polyacrylamide 0.15%-0.6%, urea phenolic resin crosslinking agent 0.2-0.3%, remaining is water.
- A kind of 6. profile control agent according to claim 5, it is characterised in that：The cationic polyacrylamide cationic polymerization Degree is more than 10%, and relative molecular weight is more than 5,000,000.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711046654.8A CN107903365B (en) | 2017-10-31 | 2017-10-31 | Urea phenolic resin cross-linking agent and synthesis method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711046654.8A CN107903365B (en) | 2017-10-31 | 2017-10-31 | Urea phenolic resin cross-linking agent and synthesis method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107903365A true CN107903365A (en) | 2018-04-13 |
| CN107903365B CN107903365B (en) | 2021-03-30 |
Family
ID=61842935
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201711046654.8A Active CN107903365B (en) | 2017-10-31 | 2017-10-31 | Urea phenolic resin cross-linking agent and synthesis method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107903365B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109401740A (en) * | 2018-12-24 | 2019-03-01 | 陕西明德石油科技有限公司 | Oil field composite modified resin is crosslinked strong gel water-plugging profile control agent |
| CN111205422A (en) * | 2018-11-22 | 2020-05-29 | 中国石油天然气股份有限公司 | Oily sludge plugging gel and preparation method and application thereof |
| CN111690399A (en) * | 2020-04-27 | 2020-09-22 | 北京大德广源石油技术服务有限公司 | Sand control agent for fracturing and use method thereof |
| CN115181229A (en) * | 2022-09-09 | 2022-10-14 | 克拉玛依市正诚有限公司 | Modified urea-formaldehyde resin cross-linking agent and preparation method thereof |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3306864A (en) * | 1962-11-29 | 1967-02-28 | Hooker Chemical Corp | Phenol formaldehyde-urea resin component binder |
| CN102336878A (en) * | 2011-07-18 | 2012-02-01 | 山东圣泉化工股份有限公司 | Low free phenol phenolic resin and preparation method thereof |
| CN102558763A (en) * | 2012-01-04 | 2012-07-11 | 山西兆信生物科技有限公司 | Foamable phenolic resin strengthening and filling material for coal mine |
| CN103122053A (en) * | 2012-09-07 | 2013-05-29 | 谢再锋 | Preparation method of urea modified phenolic resin |
| CN104073205A (en) * | 2014-06-25 | 2014-10-01 | 安徽神舟飞船胶业有限公司 | Formula and preparation process of urea improved phenol-formaldehyde resin adhesive |
| CN104479148A (en) * | 2014-12-01 | 2015-04-01 | 中国石油天然气股份有限公司 | Preparation method and application of water-soluble urea-phenol-formaldehyde resin powder |
| CN106916578A (en) * | 2015-12-24 | 2017-07-04 | 中国石油天然气股份有限公司 | A kind of high temperature resistant Weak Gels type profile control agent and preparation method thereof |
| CN107118512A (en) * | 2017-05-26 | 2017-09-01 | 江苏省江南新型复合研磨材料及制品工程技术研究中心有限公司 | A kind of phenol-formaldehyde resin modified having excellent storage stability and its preparation technology |
-
2017
- 2017-10-31 CN CN201711046654.8A patent/CN107903365B/en active Active
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3306864A (en) * | 1962-11-29 | 1967-02-28 | Hooker Chemical Corp | Phenol formaldehyde-urea resin component binder |
| CN102336878A (en) * | 2011-07-18 | 2012-02-01 | 山东圣泉化工股份有限公司 | Low free phenol phenolic resin and preparation method thereof |
| CN102558763A (en) * | 2012-01-04 | 2012-07-11 | 山西兆信生物科技有限公司 | Foamable phenolic resin strengthening and filling material for coal mine |
| CN103122053A (en) * | 2012-09-07 | 2013-05-29 | 谢再锋 | Preparation method of urea modified phenolic resin |
| CN104073205A (en) * | 2014-06-25 | 2014-10-01 | 安徽神舟飞船胶业有限公司 | Formula and preparation process of urea improved phenol-formaldehyde resin adhesive |
| CN104479148A (en) * | 2014-12-01 | 2015-04-01 | 中国石油天然气股份有限公司 | Preparation method and application of water-soluble urea-phenol-formaldehyde resin powder |
| CN106916578A (en) * | 2015-12-24 | 2017-07-04 | 中国石油天然气股份有限公司 | A kind of high temperature resistant Weak Gels type profile control agent and preparation method thereof |
| CN107118512A (en) * | 2017-05-26 | 2017-09-01 | 江苏省江南新型复合研磨材料及制品工程技术研究中心有限公司 | A kind of phenol-formaldehyde resin modified having excellent storage stability and its preparation technology |
Non-Patent Citations (2)
| Title |
|---|
| 戚勇 等: "复合交联聚合物调剖剂的室内实验研究", 《精细石油化工进展》 * |
| 李和平: "《胶黏剂生产原理与技术》", 31 August 2009 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111205422A (en) * | 2018-11-22 | 2020-05-29 | 中国石油天然气股份有限公司 | Oily sludge plugging gel and preparation method and application thereof |
| CN111205422B (en) * | 2018-11-22 | 2022-12-02 | 中国石油天然气股份有限公司 | Oily sludge plugging gel and preparation method and application thereof |
| CN109401740A (en) * | 2018-12-24 | 2019-03-01 | 陕西明德石油科技有限公司 | Oil field composite modified resin is crosslinked strong gel water-plugging profile control agent |
| CN111690399A (en) * | 2020-04-27 | 2020-09-22 | 北京大德广源石油技术服务有限公司 | Sand control agent for fracturing and use method thereof |
| CN111690399B (en) * | 2020-04-27 | 2021-09-07 | 北京大德广源石油技术服务有限公司 | Sand control agent for fracturing and use method thereof |
| CN115181229A (en) * | 2022-09-09 | 2022-10-14 | 克拉玛依市正诚有限公司 | Modified urea-formaldehyde resin cross-linking agent and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107903365B (en) | 2021-03-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107903365A (en) | A kind of urea phenolic resin crosslinking agent and its synthetic method | |
| CN104449618B (en) | A kind of heat-resistant salt-resistant high-temperature self-crosslinking in-situ polymerization water shutoff gel | |
| CN101121880B (en) | Natural macromolecule modified starch profile control agent for oil field | |
| CN102533233B (en) | High-temperature-resistant and high-salinity-resistant water-plugging profile control agent, and preparation method and application thereof | |
| CN102453473B (en) | Organogel blocking agent for water blocking and profile control, and preparation method and application thereof | |
| CN102504292B (en) | Organic cross linking system for polymer flooding and preparation method of cross linking agent | |
| Jia et al. | Evaluation of polyacrylamide gels with accelerator ammonium salts for water shutoff in ultralow temperature reservoirs: Gelation performance and application recommendations | |
| CN103554357B (en) | A kind of polymkeric substance-ionic liquid compound clay stablizer and synthetic method thereof | |
| US11427748B2 (en) | Mussel bionic gel composition, self-repairing gel, profile control and water plugging agent, method for preparing self-repairing gel, and use | |
| CN109369848A (en) | A kind of functional form temperature-resistant anti-salt plugging agent and preparation method thereof | |
| CN104140806A (en) | Modified acrylamide polymer thickening agent and preparation method thereof | |
| CN102965093A (en) | Composite crosslinking deep profile control agent for oil reservoir deep profile control and preparation method thereof | |
| CN104232071A (en) | Non-metallic cross-linking agent for ultra-high temperature fracturing fluid and fracturing fluid, as well as preparation and application | |
| CN108102099A (en) | A kind of preparation method of oil field high temperature clay stabilizer | |
| CN104357030B (en) | A kind of drilling fluid branched polymer inorganic agent and preparation method thereof | |
| CN109097014A (en) | It is a kind of to use the underground crosslinked type resin plugging agent and its application that seawater is prepared | |
| Wu et al. | Insights into the key aspects influencing the rheological properties of polymer gel for water shutoff in fractured reservoirs | |
| Shao et al. | High performance hydrophobic associated polymer for fracturing fluids with low-dosage | |
| CN111087996B (en) | High-temperature-resistant composite gel plugging agent and preparation method and application thereof | |
| CN105331345A (en) | Retarded foam gel for profile modification of oil field | |
| CN111088023B (en) | High-temperature-resistant polyacrylamide gel plugging agent and preparation method and application thereof | |
| CN104140791A (en) | Weak gel visco-shearing potentiator for drilling fluid and preparation method thereof | |
| CN106221680A (en) | A kind of preparation method of drilling fluid hydrophobic associated polymer coating agent | |
| CN111087990B (en) | High-temperature-resistant gel plugging agent composition and preparation method and application thereof | |
| CN106318369B (en) | A kind of cationic gel acid thickening agent and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |